


Other Duties As Requested

by basil_leaf



Category: Supernatural
Genre: Aftercare, Alternate Universe - Corporate, Anal Fingering, Anal Sex, BDSM, Begging, Begging Dean Winchester, Blow Jobs, Bondage, Butt Plugs, Caning, Chastity Device, Cock Slapping, Cock Warming, Come Eating, Come Marking, Come Swallowing, Comeplay, Competence Kink, Corporal Punishment, Dom Gabriel, Dom/sub, Domestic Kink, Drunken Confessions, F/F, Face Slapping, Face-Fucking, Forced Orgasm, Frottage, Gags, Hand Jobs, Kissing, M/M, Multiple Orgasms, Mummification, Nipple Piercings, Nipple Play, No Aftercare, Object Insertion, Oral Sex, Orgasm Delay/Denial, Orgasm Denial, Piercings, Play Party, Praise Kink, Punishment, Rimming, Rough Oral Sex, Rough Sex, Scratching, Semi-Public Sex, Sharing a Bed, Somnophilia, Sounding, Sub Dean Winchester, Supernatural Kink Bingo 2019, Teasing, Vibrators, Wax Play
Language: English
Status: In-Progress
Published: 2019-02-09
Updated: 2019-03-15
Packaged: 2019-10-24 20:18:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 14,149
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17710886
Author URL: https://archiveofourown.org/users/basil_leaf/pseuds/basil_leaf
Summary: When Gabriel’s assistant is out on maternity leave, Dean Winchester is sent up from the front desk to fill in.  Dean is a hard worker, eager to please, and the most attractive man Gabriel has ever encountered.  Gabriel tells himself he’s going to keep it strictly professional but a couple of sex dreams and a few too many lemon drops could change everything.*This is tagged for what I know is coming up in the fic however, additional tags may be added as I write.





	1. The Secretary

**Author's Note:**

> This was written for SPN Kink Bingo and chapter 1 fills the AU square. Each chapter title is borrowed from a movie, television show, or song title and the characters are borrowed from Supernatural!  
> —  
> “Aine” is an Irish name that, depending on who you ask, is pronounced like Anna or Anya (personally, I prefer the second pronunciation). It’s the name of a fairy queen, which suits Charlie and Gilda’s daughter, if you ask me!

“You’re sure you can’t come? Just this once?” Gabriel pled.

“Gabriel,” Charlie laughed, “Aine is barely a month old, you know I can’t. Besides, you’re the one who insisted on nine months paid maternity leave and Aine and I are taking full advantage of that. Between that and the leave Gil is going to be able to take, she’ll have one of us home for the entire first year. So, thanks for that.” Charlie was lounging on the couch in Gabriel’s office as if she owned the place, enjoying watching her boss cuddle her baby against his chest. “Are… are things not working out with Dean?” 

Charlie’s tone had shifted from joking to worried but Gabriel waved off her concern as he glanced towards his closed office door, as if Dean’s name being uttered would summon him. “Oh, yeah, I mean, no, I mean...” he replied, bouncing Aine as he cradled her in his arms in an attempt to hide how flustered the question had gotten him. “Things are working out. He’s fine, more than fine, even. Hell, I’m not nearly as lost without you as I thought I’d be but this is different. This is travel. Dean’s from the front desk, he’s never done anything like this before.” Not to mention that I want to bend him over my desk and bury myself in his ass every time he walks through that door, Gabriel added in his mind. 

Charlie rolled her eyes. “I’m not going to San Francisco with you,” she answered definitely as she pushed herself up from the couch. “I need to get Aine home for her nap and you need to tell Dean he’s got to pack for a trip next week.” Charlie packed up the few things she had brought for Aine, all of which had been quickly discarded by the little girl in favor of tugging on Gabriel’s hair and tie, and then scooped her daughter out of her boss’s arms before strapping her into her car seat. 

Gabriel walked Charlie to the door of the office. “Thanks for bringing her by,” he said, indicating the baby before he bent down and peered into the car seat. “It was so good to meet you, little lady,” he cooed as he gently squeezed one of Aine’s feet. He righted himself and then opened the door for his assistant. “Last chance for a fabulous vacation…” he tried, his voice taking on a playful lilt.

“Hell no, boss man,” Charlie singsonged right back, laughing at his antics.

Gabriel chuckled, too. “Can’t blame a guy for trying. Give my best to Gil.”

With that, the elevator arrived and Charlie stepped in, the thick door closing and sweeping mother and baby away.

Gabriel turned to his new executive assistant. “They told you there was travel involved with this position, yeah?” He asked.

Dean looked up from his computer, seemingly a little startled that Gabriel was addressing him. “Uh, yeah,” he replied. Then, after clearing his throat, “Yes, sir.”

Gabriel inwardly groaned, both at the title and at Dean’s voice - smooth and deep like a well aged scotch. He recovered quickly, though, mentally shaking himself out of it. “Well, pack your bags. We leave for San Francisco first thing on Monday.”

Dean perked up at the proclamation. “San Francisco?” He asked. “Like, San Francisco, California?” When Gabriel nodded, a grin spread across Dean’s face. “Awesome, that’s about an hour from where my brother is going to school!”

Gabriel smiled, Dean’s joy infectious. The pair had chatted some over the past month but Dean had always seemed more focused on the work aspect of things. He was clearly nervous about this rather major, if temporary, promotion but his work had been nothing but stellar so far. It seemed that Dean realized that this was his chance to make an impression and get on the short list for any future promotions. What he didn’t know what that Charlie had hand picked him as her replacement for during her maternity leave. He wasn’t going to waste this opportunity to get to know his new assistant a bit better, though.

“What’s your brother studying?” He asked, noticing how Dean’s face lit up at the question.

The man radiated pride as he told Gabriel about Sam, a first year law student at Stanford. About how smart Sam was and how he had gotten a full ride to college at Stanford and how he now had a full tuition scholarship for law school. “That’s why I work here, actually,” he confided. “Honestly, I’d rather be doing something with my hands, getting dirty under the hood of a car, but even the downstairs gig pays more than a mechanic’s salary so here I am. The kid deserves the world, so I work hard and send him everything I can so he can focus on his studies and not have to worry about finding a job.”

Gabriel was in awe of Dean. He clearly loved his little brother, something that wasn’t quite as common in his own family, and Gabriel wondered why burden of providing for Sam fell to him. Dean couldn’t be more than three or four years older than Sam. But, Gabriel realized, that line of questions likely wouldn’t have answers full of pride and joy and, so, it was for another time. 

“We’ll have to take him for dinner while we’re out there…” Gabriel began but Dean interrupted.

“Oh, I couldn’t drag you into this, sir. I’ll probably take a bus down one night after we’re done and eat with him in the cafeteria.” 

Gabriel was appalled at the idea. “Why would you…” his voice trailed off. “Dean, you’ve never been on a business trip before, have you?” When the younger man shook his head ‘no’ Gabriel smiled. “You’ll have a per deim - a set amount that you can spend each day on things like food, drinks, and snacks. Charlie and I usually share a room, which allows us to bump our per deim to $75 each. But, for a meeting with a budding young lawyer, well, that’ll come from the recruitment fund.”

Dean looked up at Gabriel with wide eyes, clearly thrown off by this turn of events.

“Find out if 7 on Thursday works for him. We like to have the best lawyers in the country on retainer. If your brother is even half as smart as you say he is, I want to have him on our team before our competitors even think about recruiting him.”

Dean nodded dumbly, a small smile playing on his lips. “Thanks, Gabe.”

Gabriel arched a surprised eyebrow at Dean, not expecting to hear the nickname coming from him after he’d been so formal for the past month.

“Sorry… I just, I heard Charlie call you ‘Gabe’ when she arrived earlier. I didn’t think… Sorry, sir. Thank you, sir.”

Gabriel chuckled at Dean’s discomfort, ignoring the tightening in his groin that it was creating. “When it’s just us, Gabe is fine, Dean.”

Gabriel returned to his office. He considered stepping into his bathroom to jerk off but, instead, opted to sit down and try to get some work done as he attempted to will his erection away. If he couldn’t get through just a conversation with Dean without having to take himself in hand, there was no way he’d make it through this trip. Gabriel busied himself with menial tasks while his erection slowly flagged and once he had a clear head and a soft dick, he turned to polishing the proposal and presentation he would be giving in San Francisco.


	2. Let's Go To Bed

**Summary for the Chapter:**

> Gabriel and Dean go on their business trip. Gabriel learns that Dean does not like flying so he helps him through the flight. When they arrive at their hotel room, they're surprised by what they find there. There's more D/s relationship building but still no smut in this chapter (it's coming, I promise).

**Notes for the Chapter:**

> This was written for SPN Kink Bingo.   
> SPN Kink Bingo square filled: Bed Sharing

The rest of the week flew by. Gabriel stayed mostly sequestered in his office, sending Dean out to pick up his lunch most days and even a dinner or two, as well. Working for his father had its perks but there were always the grumbles of nepotism when Gabriel would get sent on a big trip like this, even after he had transferred from the home office, and Gabriel knew he needed to deliver if he was going to keep the whispers to a minimum. He couldn’t just be good at his job, he had to be great and so he devoted every moment he could to making sure this trip would go off without a hitch and that he’d be coming home to Lawrence with a new account. 

Bright and early on Monday morning, the car arrived for Gabriel. He put his bags in the trunk, making sure to lie his suits flat, and hopped into the back of the SUV, where Dean was already seated. Gabriel handed Dean a travel mug and his assistant gave him a questioning look. 

“I thought the secretary was supposed to fetch coffee for the boss?” he joked, his voice deeper and more gravelly than Gabriel had ever heard it before.

Gabriel shrugged. “Whenever we travel, Charlie claims that it’s my fault that she has to be up so early so that makes coffee my job. It’s black but if you’ve just got something against the creamer we’ve got at the office, there’s enough time to run inside.” Gabriel kept his voice as nonchalant as possible. Sure, Dean’s coffee preferences seemed as simple as possible but Charlie’s hadn’t been much more involved but Gabriel hadn’t paid attention and he’d gotten it wrong for weeks.

They made the rest of the ride to the airport in relative silence, both men sipping on their coffees. The closer they got to their destination, the more antsy and grumpy Dean seemed to become and Gabriel couldn’t help but shoot him questioning glances, which the younger man steadfastly ignored. 

By the time they made it through the security checkpoint, Dean was downright surly and Gabriel had finally had enough. “What’s going on with you, Dean-o?” Gabriel asked, keeping his tone conversational.

Dean shrugged him off. “Nothing. I’m fine,” came his curt reply as he walked away, his long strides putting distance between the two men as they walked toward their gate

Gabriel was in shock for a moment at Dean’s behavior before he collected himself and caught up with the taller man. It had been a long while since anyone had used a tone of voice like that with him and it wasn’t a behavior that Gabriel was going to let slide. He grabbed Dean’s arm and pulled him into an alcove near a vending machine. “What the hell is wrong with you?” He asked, using what he had come to call his ‘dom voice.’

It seemed to have the desired effect of pulling Dean out of his head a little. The taller man took a step back and looked to the floor for a moment before meeting Gabriel’s stare. “I just don’t like flying, ok?”

Dean’s words turned out to be an understatement. At one point, he was bouncing his leg so hard that it was shaking Gabriel’s seat. Gabriel reached over and put a hand on his assistant’s knee, surprised but happy to feel when Dean relaxed into the touch. As soon as they boarded the plane, though, all bets were off. Dean gripped the armrests like his life depended on it and as soon as the flight attendant came to ask if they would like a drink before takeoff, Dean ordered a whiskey. 

It was early, so the flight attendant raised his eyebrows at the request.

Gabriel placed his hand on Dean’s knee again, hoping to be a reassuring presence. “He means an Irish coffee, please. And I’ll just have regular coffee, black with two sugars.”

Gabriel kept an eye on Dean’s alcohol consumption during the flight. He didn’t want Dean to freak out but he also knew that they had their first meeting of the trip about 2 hours after they landed and he needed Dean to have his wits about him. He ended up deciding to cut Dean off about half way through the flight, after the man tried to order his fourth drink of the morning. 

Dean shot Gabriel a look that could only be described as a glare, maybe even a bitch face…

“Dean, I’m going to help you relax without the booze,” Gabriel assured his assistant. “I want you to close your eyes and breathe.” He paused for a moment, raising an eyebrow at Dean until he did as requested. “Breathe in… one… two… three… four… hold it for one… two… three… four… and breathe out for one… two… three… four…. Good, Good job Dean. Keep breathing like that for me. In, one… two.. three… four…” Gabriel kept his count up for Dean for another couple of breaths.

“I’m going to touch you now, Dean; just your hand. If you want me to stop, just say so.”

Dean took another deep breath. “Everything inside of me is screaming at you to stop now but I don’t know if I really want you to do that.”

Gabriel closed his own eyes and pinched the bridge of his nose before proceeding. He spoke carefully, knowing that he was wading into dangerous waters. “What if... what if ‘no’ didn’t mean no? What if there was another word, something that might not come up in regular conversation, that told me you wanted me to stop? Is there a word that you can think of that we could use?”

Dean thought for a moment, his eyes still closed. “Impala,” he finally said. “As long as you don’t ask me about mechanics or my car, that should work.” 

Gabriel nodded before he remembered that Dean couldn’t see him. “Impala, great. From now on, ‘stop’ and ‘no’ don’t mean anything. Instead, if you really want me to stop, say ‘Impala,’ alright?”

Dean nodded.

Gabriel pried Dean’s hand off of the arm rest between them. He held his assistant’s hand, palm up, and began to massage it. He held Dean’s thumb in one hand and pressed down on the center of his hand with the other. “When I message the center of your hand like this,” he told Dean, “it helps you to calm your mind and holding your thumb like I am helps to relieve anxiety and worry.” Gabriel shifted his grip to Dean’s forefinger, giving it a good squeeze. “This finger helps alleviate fear.” Gabriel slowly moved through Dean’s fingers, explaining how each could help to calm him - middle finger for anger, ring finger for depression and sadness, and pinky finger for increase optimism - as he discretely checked the man’s pulse between. His heart rate was evening out, which pleased Gabriel, and he continued to hold and massage Dean’s hand, starting with his thumb once again, stroking and rubbing this time instead of holding and squeezing.

After he finished with Dean’s first hand, Gabriel reached across to give his other hand the same treatment. It seemed to be working, the breathing or the hand massage, or a combination of both, were having an effect on Dean. All was going well until the plane hit some major turbulence.

“Fuck,” Dean hissed, his eyes squeezing shut even tighter than they had been before. His hand gripped Gabriel’s like a vice but, instead of pulling away, Gabe let it happen. 

“Keep breathing for me, Dean,” Gabriel instructed, “you’ve got this. You’re such a strong man, grip my hand as tight as you need to but know that you’re going to get through this. Breathe with me.” Gabriel regulated his breathing to the speed that he wanted Dean to follow and, soon enough, they were through the turbulence and Dean was starting to relax again. 

Dean was quietly humming something, his eyes still screwed shut and his jaw occasionally clenching, but the tension had leached out of his shoulders and torso, which Gabriel counted as a win.

Still, when the plane landed in California, Dean was immediately on his feet and ready to practically run off of the aircraft. Gabriel had kept a calming hand on Dean’s body - either his shoulder or his knee depending on the moment - but the younger man shook it off in favor of getting to his feet. He practically pulled Gabriel off of the plane when it was their turn to disembark.

Gabe had to smile. It was kind of annoying but, for some reason, he also found it adorable. 

The men collected their bags and got into the car that was waiting to take them to their first meeting of the day. The day flew by. Gabriel was being treated like a king as he wined and dined the executives that they were visiting and Dean was happily riding his coattails. Gabriel often caught himself looking fondly at his assistant. Charlie had always been great on these trips but Dean was something entirely different; his charm and charisma were a perfect match for Gabriel’s humor and by the end of the first night, Gabriel was all but certain that they had this merger in the bag without even giving his presentation. Dean’s presence made what would have been a obligatory work function into an enjoyable evening out but eventually the night had to end and the pair found themselves outside of their hotel. 

Check in went thankfully quickly and a chipper bellhop led them to their room. He swiped the key card and put their bags down. “Would you like me to turn down the blanket for you, sir?”

Gabriel declined, dismissing him with a generous tip. 

He picked up his bag and motioned Dean into the bedroom, intending to let his assistant take the first pick of beds. However, Dean stopped short in the doorway and Gabriel ran into him. 

“Dean?” Gabriel asked, nudging him in the back.

Dean stepped forward, allowing Gabriel to see into the bedroom. “There’s got to be a mistake.”

There was only one bed in the room, instead of the two that the men had anticipated. 

“Huh…” was all Gabriel could say. He would be happy to share the bed but, clearly, Dean wasn’t interested in that. He put his bag down and crossed to the phone beside the bed. “I’ll just call down to the front desk and get it sorted out.” He picked up the receiver and punched a few buttons. “Yeah, hello, This is Mr. Shurley, currently in room 732. I’m afraid there’s been a mistake. We’re supposed to have two queens in our suite,” Gabriel paused and winked at Dean when he said ‘two queens,’ “but we’re in a king suite.”

Gabriel listened for a moment, humming at the appropriate moments. “So, that’s it? Really? Alright, well, thank you.”

Dean picked up his bag as Gabriel hung up the phone. “Where are we headed?” He asked.

Gabriel smiled up at Dean. “Uh, well, we’re going nowhere. Apparently, there’s a convention this week and the hotel is completely booked.”

Dean stared at his boss, his eyes wide. “You’re telling me that in this entire hotel, there isn’t one single open room?” He looked at Gabriel with disbelief. 

“Nope,” Gabriel replied, popping the ‘p.’ “It’s this room or no room.”

Dean walked back into the sitting room. “Guess one of us is on the couch, then.”

Gabriel followed him into the main room and laughed. “You’re too big for this thing. There’s no way you’d get any sleep out here.” Gabriel scanned the room, there wasn’t really the space for a rollaway bed, there was really only one option and he turned to tell Dean that.

Dean was giving Gabriel a pointed look. Like he thought that… “Oh, oh no. There’s no way. I am not sleeping on that thing.” Gabriel could barely get through his sentences without giggling like a schoolgirl at the thought of spending even one night on a couch. “Dean, the bed in there is huge,” he said said, indicating the bedroom. “We can just share the damn thing. It would be ridiculous for either of us to sleep out here. If you really want to, we can set up a pillow wall between us,” he joked. “Let’s just be adults about this and share.”

Dean looked at the couch one more time before turning his gaze on Gabriel, who couldn’t help but notice the pink tinging his assistant’s cheeks, making his green eyes pop even more than they usually did. Dean bit his lower lip and nodded. “Yeah,” he breathed, “yeah, let’s do that.”

Gabriel was certain he imagined Dean’s hooded eyes as his assistant turned away from him and walked back into the bedroom. Gabriel waited until he heard the bathroom door close before following Dean into their bedroom. He quickly changed into his pajama pants and contemplated leaving his undershirt on but decided that if he was going to get any sleep, he needed to be as comfortable as possible and pulled the thin fabric over his head. 

Dean emerged from the bathroom wearing his T-shirt and boxers, the blush that lingered on his cheeks deepening when he saw Gabriel shirtless. 

Gabe smirked at him as he brushed by on his way into the bathroom to take care of his nightly routine. 

The pair climbed into bed, Dean so close to the edge that he looked like he was about to fall out, and each turned his back to the other.

**Notes for the Chapter:**

> Thank you for reading! The comments and kudos on chapter one were much appreciated! I'd love to hear how much you're enjoying the fic!


	3. Requiem for a Dream

**Summary for the Chapter:**

> Gabriel wakes up in the middle of the night only to learn that Dean is quite the cuddler. He uses this to his advantage and teases Dean in his sleep.

**Notes for the Chapter:**

> In this chapter, Gabriel is physically touching Dean in a sexual manner without permission while Dean sleeps. If this is something that might bother you, I’ll include the major plot points in the end notes. After this chapter, safe words are in place and concent is either explicit or implied throughout the rest of the story.
> 
> SPN Kink Bingo Square Filled: Teasing

Gabriel woke up unsure of what time it was. The room was still dark but, then again, they had drawn the blackout curtains before going to bed, however the phone wasn’t ringing with his wake up call so Gabriel assumed it was still rather early. He was very warm and tried to stretch out and move the blanket but realized quickly that he couldn’t move. Something or, rather, someone was holding him in place. 

Dean, it would seem, was a cuddler. 

Gabriel felt his body immediately start to react to this realization but he fought against his rapidly filling erection. That is, until he realized that Dean was sporting an impressive almost-morning wood himself. Then, when the taller man nuzzled into Gabriel’s hair, he had an idea.

Gabriel knew he shouldn’t, he knew that this was a sexual harassment case waiting to happen but he couldn’t help himself. He shifted his hips back into Dean’s crotch a few times, rocking against his assistant’s cock and teasing the man in his sleep.

After a few rocks, Dean groaned and his arms tightened around Gabriel pulling him in even closer. Gabe pushed backwards, trying to wedge Dean’s cock between his ass cheeks, even through his pajama bottoms and the man’s boxers. He didn’t succeed - too much fabric and not enough leverage - but he did get Dean to start humping him, more quiet moans falling from his assistant’s lips as he slept.

Gabriel began rolling his hips in a circular motion and he could feel Dean’s breath pickup, soft puffs of air blowing across the back of his neck. Gabriel was so hard, now, knowing how he was affecting Dean, but the way the younger man was holding him, he couldn’t reach his own cock to do anything about it. Gabriel bit his lip, holding in his groan (his of frustration), as he continued to tease Dean.

Suddenly, Dean tensed and all movement stopped. Gabriel stilled his hips, as well, wondering what had happened. 

“Shit,” Dean whispered, carefully extracting himself from Gabriel, who had closed his eyes as soon as he had heard the younger man’s voice.

Gabriel felt the bed shift as Dean stood. He heard him walk across the room and into the bathroom, followed by the sound of the shower running, muffled by the bathroom door. Gabe flipped onto his back and scrubbed a hand down his face. He had almost been caught and that would have been disastrous. As it was, Dean would probably want to go home and be reassigned back to the front reception desk. Gabriel had only known the man for a few weeks but the thought of that was already painful. He was hot and obviously submissive but, more than that, Gabriel had come to like Dean as a person and a colleague and he would miss that. Besides, Charlie wouldn’t be around to train another new assistant like she had with Dean. 

That train of thought had made Gabriel’s erection flag and he turned onto his stomach, burying his head in his pillow as he tried to sleep again. Morning would bring consequences, he was sure, and he’d rather be oblivious to the world around him until that time came.

—

The phone rang, pulling Gabriel from a fitful sleep. His hand reached blindly for the source of the noise, finally landing on the phone’s receiver. “Yeah?” He asked, his voice groggy.

“Mr. Shurley, Mr. Winchester, this is your 6 AM wake up call,” a cheerful voice responded.

“Yeah. Thanks.” Gabriel sat up, noticing that Dean wasn’t beside him and the memories from the night before flooded back. “Fuck,” he muttered as he swung his legs over the edge of the bed and onto the floor. The bathroom door was open so Gabriel padded inside and took care of his morning routine. 

While he was finishing up, he heard the door to their room open and slam shut. 

Gabriel dressed quickly, figuring it was better to have this conversation now, rather than to put of the inevitable. He exited the bedroom only to stop dead in his tracks just beyond the doorway. 

Dean was dressed for work, sitting at the table in their kitchenette with two cups of coffee and a spread of fruits and yogurt on the table. He handed one of the cups to Gabriel. “Milk and 2 sugars, right?”

Gabriel nodded dumbly. His eyes darting from Dean to the table and back again. “Th- thank you,” he finally managed. 

“I, uh, I woke up early so I got us some breakfast, I hope that’s alright.” Dean blushed and ducked his head as he spoke and Gabriel thought it was adorable.

Hot, submissive, and attentive… the man was perfect and Gabriel was totally and completely screwed.

The rest of the day passed without incident. Early in the afternoon, Gabriel made his pitch, which went over extremely well, and then he and Dean were excused for the rest of the day while the executives pondered the options in front of them. Gabriel was even more certain, now, that he had nailed it, though, and that he’d be going home with a new subsidiary coming in under the wing of his father’s company.

The pair drove out to Stanford, Gabriel letting Dean take the wheel as they zipped along the highway towards his brother. Dean’s excitement was contagious and Gabriel found himself laughing and singing along to the oldies station his assistant had found on the radio, despite the fact that he had tried to switch it to something more current. Dean had batted his hand away from the dial, though, with a terse “Driver picks the music, shotgun shuts his cakehole.” Dean’s eyes hadn’t matched his tone, though, the mirth and joy shining through.

Dinner was a delightful affair. Dean’s eyes shined with pride when he introduced Sam to his boss and both of the Winchesters’ eyes practically bulged out of their heads when Gabriel told them where he had made reservations for their meal. 

Sam and Gabriel shared a bottle of wine while they ate, Dean opting for beer, and Gabriel was thoroughly impressed with the younger Winchester’s wit and intelligence, not to mention his looks. If he hadn’t already had his eyes set on Dean, Gabriel would definitely have attempted to spend the night in Sam’s apartment. Where Dean seemed to be naturally submissive, Sam came across as more dominant at times, more like a gentle dom or, even better, a switch. However, Gabriel’s more submissive days were mostly behind him; Dean was much more his type.

Gabriel shook his head, banishing the thought. It didn’t matter which Winchester was his type because he wasn’t going to have either of them. Dean was his assistant and Sam his assistant’s brother. Gabriel might be a hedonist but he wasn’t that much of a horn dog that he couldn’t keep it in his pants for one lousy business trip.

The rest of dinner passed without any incident and before Gabriel even realized it, it was nearly 11 at night and they were outside of Sam’s apartment once again. “Seriously, kiddo, I’m going to keep an eye on you and when you graduate, there’s a place for you in our legal department if you want it. You’re sharp and I like that.”

Dean was practically vibrating after the dinner with Sam so Gabriel took the wheel on their drive home, parroting Dean’s warning about the music back at him when he grumbled about the Taylor Swift playing on the station that Gabe had selected. By the end of the song, though, Dean’s head was bobbing along and Gabriel caught him mouthing the words to the chorus out of the corner of his eye.

When they got back to their hotel and up to their room, though, everything changed. Dean froze in the doorway for a second before stepping in. “I think I’m gonna crash on the couch tonight,” he said and Gabriel could tell he was trying to keep his voice nonchalant. 

“Why would you do that? Sharing was fine last night and there’s no way you’re gonna fit on the couch, big guy,” Gabriel reminded him. “Besides, I’m still kind of wired, thought I might stay up and watch some tv or something.” Gabriel had no plans to actually do that but he wanted - no, needed - to have Dean in his bed again.

Dean ducked his head and blushed. “Oh, okay,” he agreed, letting out a puff of air from his mouth. He turned and strode into the bedroom, disappearing from Gabriel’s sight.

Gabriel flopped down on the couch, actually feeling rather exhausted after the presentation and the night out with the Winchesters. He flipped on the tv and flicked his way through the channels a few times, not finding anything to hold his interest. There was a medical drama, a police procedural, some kind of sitcom, and a weird Japanese game show that got him to pause for a couple of rounds but, with a yawn, he turned off the television and just hoped that he had killed enough time for Dean to be comfortable in the bed.

Luckily, Dean was tucked under the covers with his eyes shut when Gabriel entered the room, quietly crossing to brush his teeth and then slipping into the bed beside him. Dean had his back to the center of the bed and Gabriel laid facing the same direction, wanting to be facing towards the younger man should he end up ensnared in his arms again. He did his best to stay awake, his eyelids getting heavier with each passing minute, in the hopes that he would be able to maneuver himself into a more favorable position if, and hopefully when, the cuddling began.

He was about to drift off when Dean shifted on his side of the bed, causing Gabriel’s eyes to dart open.

Dean was now laying on his back closer to the center of the bed, one of his arms reaching out toward Gabriel. 

Gabriel shifted closer, still facing Dean, and waited. Eventually, Dean rolled over and into Gabriel’s space. One of his hands landed on Gabriel’s hip before snaking around to rest on his ass. Gabriel wrapped an arm around Dean, as well, this time, and rested his forehead against the larger man’s shoulder. He could feel Dean’s cock start to gain interest at the contact and Gabriel smirked, thrusting his hips forward gently to encourage it. Dean groaned in his sleep and then mumbled something that made Gabriel’s eyes go wide.

“Gay...brl”

It couldn’t be his name… Sure, it sounded like Dean had just said Gabriel’s name in his sleep but it had to be something else, right? Gabe’s mind whirled through possibilities of what Dean could be dreaming about but as Dean’s hips began to thrust, his cock rutting delightfully against Gabriel’s, he said it again, this time as a whine.

“Gabe… fuck… please…”

Dean was having a sex dream, Gabriel realized, about him. 

Fire shot through Gabriel’s veins at the notion and Gabriel quietly groaned Dean’s name, as he began thrusting forward again, in time with Dean’s hips, until both of them were panting. 

“So close,” Dean slurred, “‘M so close… please… please lemme...”

Dean’s begging, even in his sleep, rocketed Gabriel so very close to the edge of his own release. The hand that wasn’t wrapped around Dean’s torso shifted lower to better align their erections as Gabriel whispered, “Do it, Dean. Come for me.”

Dean’s body went tense as he let out one final groan, releasing into his boxers. Gabriel was able to hold his own orgasm at bay just long enough to slip out of Dean’s now pliant arms and into the other room. He grabbed some tissues and jerked himself off, quietly whimpering his assistant’s name as he came.

Gabriel flopped down onto the couch and turned on the tv again, determined to fall asleep upright and with the television on so that Dean wouldn’t have any idea what had happened - or be nearly as embarrassed about what he could piece together - when he woke.

**Notes for the Chapter:**

> Major Plot Points:  
> \- Dean is a cuddler  
> \- Gabriel gives the presentation, it goes very well  
> \- Gabriel and Dean take Sam out for dinner  
> \- Dean has a sex dream about Gabriel


	4. Drunk In Love

**Summary for the Chapter:**

> Dean and Gabriel spend the last night of their trip celebrating with good food and booze.

**Notes for the Chapter:**

> This fills the Drunken Confessions square of my kink bingo card!

Gabriel’s cell phone rang as he and Dean were finishing up breakfast. “Hey-a pops, I’ve got my hands full right now so I’m gonna put you on speaker phone, what’s up?” Gabriel greeted as he placed his phone down on the table, hopeful that his father was calling with good news.

“I just got off of a call with Mr. Rannigan in San Francisco. Looks like you did it again, kid, they’re accepting our offer to purchase and merge their company into ours.”

Gabriel beamed across the table at Dean as his father spoke. 

“You’re set to meet with a couple people over there throughout the day to sign the papers and finalize everything. My assistant emailed everything to yours. How’re things working out with that, by the way? Charlie’s still on leave, right? I’m still not convinced that you should have taken one of the front desk people, no matter what Charlie said about him...”

Gabriel rolled his eyes at Dean, of course his dad wouldn’t care that the assistant in question could hear every word. “Dad,” he interrupted, “Dean’s great. The man can schmooze with the best of ‘em and he’s a big part of why things ran so smoothly this week.” Gabriel winked at Dean, loving the blush the compliments were bringing to his assistant’s cheeks. He continued to praise Dean throughout the rest of the phone call in subtle (and some not so subtle) ways, as the man checked his email for their itinerary for the day.

Dean grabbed Gabriel’s attention with a wave, showing him that their first meeting of the day was scheduled to start in an hour. 

Gabriel mouthed the words ‘thank you’ to Dean before bidding his father farewell so that he and Dean could get ready for their meeting and promising to call as soon as he was back in the office in Lawrence. 

Gabriel and Dean quickly got ready for the day and called an Uber to take them over to Treats and Tricks Publishing, the newest subsidiary of Shurley Publishing House. Or, at least, that’s what it would be in a couple of hours.

The men talked easily in the car, the conversation flowing freely, and Gabriel marveled at the man who had, among other things, so quickly become his friend. They bantered back and forth, Dean teasing Gabe for his pampered upbringing and Gabriel hitting back by wondering aloud how Sam had come to be so cultured as compared to his older brother. 

The ride passed quickly and the pair were whisked into the building. The CEO and Chair of the Board were both waiting for them in the lobby and Gabriel chucked a bit at how adorably quaint it was. The only reason he and Dean were still even in town to take care of the paperwork in person was because the deal closed earlier than Gabriel and his dad had anticipated. They had expected meetings and negotiations to occur throughout today but they certainly weren’t complaining about this particular turn of events. 

The signing went without a hitch. The photographer (and Gabriel was still surprised by that addition to the proceedings; this was a merger, not an international peace treaty) accidentally mistook Dean for an executive and had him stand beside Gabriel in the official photos. He’d likely get an earful from his dad and a ribbing from at least one of his brothers about it but he couldn’t find it in himself to care. Honestly, Mike and Luci would probably love that they’d eventually be able to talk down about “the idiots at the San Francisco branch.” Gabriel just loved that Dean seemed to be enjoying himself. Besides, Dean was dressed the part so why not pretend for a day that he was interested in his work peer and not his direct subordinate.

Gabriel began referring to Dean as “Mr. Winchester” throughout the rest of the day’s proceedings and with each utterance of that name, Dean blushed a little. Luckily, the San Francisco executives didn’t seem to notice but, rather, treated Dean with more and more deference throughout the day. At one point, the CEO wondered aloud if “perhaps Mr. Winchester would like to sign one of the ceremonial contracts?”

It took everything in Gabriel not to laugh. He wasn’t trying to humiliate the execs from TNT, he was just enjoying the way that the praise and faux promotion made Dean react. “Unfortunately, my father is rather particular, even in ceremony, about having the Shurley name on the documents,” he lied quickly and smoothly, winking at Dean. “Mr. Winchester is one of our nuts and bolts guys. He really enjoys getting under the hood of a deal and working out the kinks; getting his hands dirty.”

That night at dinner the drinks were flowing. Gabriel and Dean had decided to stay in the hotel bar for their meal and neither were regretting their decision. The burgers were delicious and they had Gabriel’s favorite brand of whiskey, which he insisted that Dean try, too.

“Woah…” Dean had sighed after just one sip. 

“Yeah,” Gabriel laughed, “it’s way better than the cheap stuff you were going to order. We’re celebrating! The tab’s open and on me.”

They chatted and drank their way through dinner and late into the night. Dean couldn’t stop talking about how embarrassed he had been when Gabriel was talking him up to the folks at TNT but, also, how good it had felt to have their respect, even though it was under false pretenses. 

“Seriously, Dean-o,” Gabriel replied through a mouthful of fries, “you were great in there. I wasn’t kidding when I told my dad that you had potential to move upstairs this morning - and I didn’t mean as an assistant. You’re charming as fuck and the way you handled yourself at the dinner on Tuesday night… I seriously think you’re a huge part of why the deal closed so quickly.”

The pair ate and drank, Dean squirming under Gabriel’s praise, which only caused the older man to heap even more on him. He loved the way that Dean reacted to his words. 

After dinner, Gabriel switched over to lemon drop martinis and Dean had a field day making fun of him for it. Every time he ordered another drink, Dean would make a jibe, ardently refusing to try the concoction. 

“Say what you want, these’re delicious,” Gabriel slurred as he sipped on his fourth - or maybe fifth? - lemon drop, “‘n’ unlike some people, I’m plenty secure in my masculinity to not be... not be bothered by your jokes.” He grinned at Dean, who was still drinking whiskey. 

Gabriel’s eyes wandered around the room for a minute, a comfortable silence falling between him and Dean. Being here, drinking with Dean, it all felt so right and Gabriel felt an overwhelming desire to let him know that.

“You know,” he whispered conspiratorially, “usually on a night like this Charlie ‘n’ I get hammered and I find someone to sleep with. Celebration sex, y’know?” 

Gabriel watched Dean’s face fall at his admission and he quickly scrambled to correct the man’s assumption. “I don’t… I don’t wanna do that tonight. I wanna be here with you. I only wanna sleep with you.” Gabriel tripped over his sentences in his haste and it was only after the words had come out of his mouth that he realized what he had said. “I mean… I mean like…” he tried but, instead, he dissolved into a fit of laughter and Dean was giggling right along with him. 

Dean threw back the rest of his whiskey and waved over the bartender, ordered them another round through his laughter. “I prob’ly shouldn’t say this ‘cause we’re sharin’ a bed and all but I had a sex dream las’ night,” Dean whispered through his giggles. 

Gabriel feigned surprise and tried to encourage his friend to keep talking. “Almost makes me sorry I fell asleep on the couch,” he said, nudging Dean’s shoulder with his own. “Who’s the lucky lady?” He wanted nothing more than for Dean to tell him the truth but he also didn’t want to make him uncomfortable and, since Gabriel wasn’t supposed to know about Dean’s dream, misgendering it seemed to be an obvious and appropriate tactic to his drunken mind.

Dean blew a breath through his lips, making a sound similar to a revving engine before he tilted his head back, his whole body engaging in his laughter. “Not a lady, Gabe. I haven’t been with a lady since… high school maybe? Rhonda Hurley in senior year… She… she made me,” Dean was giggling again and the words wouldn’t come out.

Gabriel was able to make something out about pink satin panties and how soft they were. “Dean, did you… wear her panties?” he asked carefully, a smirk sneaking onto his lips.

Dean laughed again and nodded his head. His eyes scrunched up and his grin showed off most of his teeth and Gabriel had never thought the man more beautiful. 

Gabriel put a hand on Dean’s leg, a little higher up on his thigh than perhaps he should have but Dean didn’t seem to mind. He leaned in conspiratorially. “Were you wearing panties in your dream last night, Dean?” 

Dean’s eyes went wide and he shook his head a little. “Yeah,” he whispered, “I think, I was. Until you ripped them off and fucked me.” Dean’s eyes went impossibly wider as he realized what he had just said and one of his hands shot to his face, covering his mouth. “I shoudn’t’ve said that,” he mumbled, his words muffled by his hand.

Gabriel grinned at Dean and gave his thigh a squeeze before sliding his hand further up the man’s leg. “Maybe not but I’m glad you did,” he whispered, right into Dean’s ear, nipping at the shell as he spoke. “Really, really glad.” 

Gabriel twined his fingers through Dean’s hair and gave a little tug. The moan that fell from his lips spurred Gabriel on as he leaned in to kiss him, his lips tracing Dean’s jaw line down from his ear until he reached the man’s mouth. 

Dean started kissing back almost immediately, for which Gabriel was grateful, his hands landing on Gabriel’s thighs. He leaned into the kiss but let Gabriel take the lead, matching the pace that the smaller man was setting.

Gabriel licked at Dean’s lips before sucking his plush bottom lip into his mouth and gently biting down. Dean’s gasp allowed Gabriel’s tongue to sweep into his mouth and Gabriel took full control of the situation. The hand he had in Dean’s hair tugged his head into the position that Gabriel wanted and his other hand grasped a handful of his shirt. He pulled Dean to his feet, in closer to his body, and his hand strayed towards the buttons on Dean’s shirt. 

Gabriel popped the first two buttons open before the sound of someone clearing their throat interrupted. He pulled his face back from Dean’s and turned to see the bartender looking at them with a raised eyebrow. “I don’t care about the kissing but you can’t get naked down here. That’s what your room’s for.”

Gabriel turned back to Dean who looked embarrassed but also on the verge of laughter again. He threw a couple of bills down on the bar - more than enough to cover their tab and buy the bartender’s forgiveness with a rather generous tip - and grabbed Dean’s hand, pulling him out of the bar and towards the elevators. 

They were blessedly alone in the small compartment and as soon as the doors shut, Dean crowded back into Gabriel’s space. He captured Gabriel’s lips again and then shifted his attention to the smaller man’s neck.

Gabriel threw his head back and groaned at the things Dean’s mouth could do and wondering what it would feel like to have the man’s lips and tongue exploring other parts of his body. However, when he caught a glimpse of himself in the polished metal of the elevator's wall, everything came crashing down on him. God, he was so drunk he could see it, even in the shitty reflection of the elevator wall.

Before he had a chance to do anything, though, the elevator stopped at their floor and it was Dean’s turn to drag Gabriel down the hall. He fumbled with the keycard, solidifying Gabriel’s resolve that he needed to put a stop to this.

Gabriel put a hand on Dean’s shoulder, swiping his own key along the magnetic lock and letting them into the room. Immediately, Dean began to take off his clothes but Gabriel grabbed his wrists as the door shut behind them. “Dean, we need to stop.” 

Dean stilled, holding Gabriel’s gaze for a moment before he turned his face away, embarrassment once again creeping into his features. 

“I want you right now, so much,” Gabriel tried to assure his assistant and Dean’s eyes landed back on his him.

“I want you, too. Want you so bad. Please fuck me? Please?”

Gabriel squeezed his eyes shut. He loved it when a sub begged for him and he nearly gave in right there, the alcohol diminishing his resistance but he knew better. “We’re wasted, Dean. I don’t want you to regret this in the morning. Go to bed.” Gabriel used the most commanding voice he could muster for the last three words and prayed that it would work.

He watched as Dean’s face fell and his shoulders slumped. Dean turned away from him and practically ran into the bedroom like a scared dog, slamming the door shut behind him.

Gabriel was simultaneously grateful to see him go and scared that he’d ruined everything. He knew it had been the right thing to do but he hoped that if Dean even remembered anything from the night, he would understand in the morning.


	5. Airplane

**Summary for the Chapter:**

> Gabriel and Dean fly home on the Shurley family jet and Gabriel figures out the best way to distract his assistant while they're in the air.

**Notes for the Chapter:**

> This was written for @spnkinkbingo and fills my Rough Sex square (aka, we've finally made it to some real smut!).
> 
> Also, while I was writing, I accepted a dare to include "a literal plot bunny" in the fic so I hope you find that part as funny as I do!

“Gabriel, where are we?” Dean asked, his voice cautious. It was the day they were scheduled to fly home, they were carrying their bags, and he knew they were in the general area of the airport.

Gabriel smiled up at Dean. “We’re on our way home but, after the flight here, I had an idea,” he explained. “So, I called my dad and figured everything out. We still have to fly but I thought that this might be at least a little more comfortable for you.” They stepped out of the hangar they had been walking through and onto the tarmac where the Shurley family private jet was waiting for them.

Dean looked up at the small plane with a mix of fear and awe. 

“It’ll just be us, the pilot and one attendant on board,” Gabriel told Dean, indicating that he should head up the steps into the plane. He followed Dean up and pushed him through the door, slinging his bag onto one of the chairs before taking Dean’s bag from him and tossing it beside his own. “Keep moving towards the back, Dean-o, that’s where we’re going to spend most of the flight.”

Gabriel had a plan and he hoped it wouldn’t backfire. 

Dean had been suspiciously quiet for most of the morning, packing his bag and refusing to look at Gabriel for longer than he had to. Gabriel had a sinking suspicion that he remembered everything from the night before but what he had really held onto was the ultimate rejection that Gabriel had given him. 

After Dean had slammed the door to their bedroom, Gabriel had spent a second night on the couch, not wanting to tempt himself with the warm, cuddly body that he had known would have been waiting for him in the bed. He knew it had been the right choice but the way Dean had treated him throughout the morning almost had him regretting the decision.

On the plane, Gabriel snuck around Dean and grabbed the man’s hand, relishing how much larger than his own it was. He paused briefly at the door, taking a deep breath and praying that Dean had been serious the night before and that the dismissal hadn’t hurt him too much. Gabriel walked through into the plane’s bedroom, pulling Dean in behind him before spinning them and pushing his assistant onto the bed. 

“I meant what I said last night, Dean. I want you and I’m used to getting what I want.” Gabriel pulled his tie off as he spoke, whipping it from around his neck. “Put your arms above your head.” Gabriel crawled onto the bed as Dean did as he was told, too shocked to ask questions. He tied his tie around Dean’s wrists, looping it through a hook on the wall above the bed - it was probably designed to anchor something in the room place in case of extreme turbulence - and then leaned in. He nibbled Dean’s earlobe and then roughly whispered, “Remember on the flight here? We decided that ‘no’ doesn’t mean ‘no’ anymore?”

Dean nodded.

“And what word did you choose instead?” Gabriel asked.

Dean swallowed hard. “Impala,” he croaked.

“Good boy,” Gabriel praised, loving the flush that crept up on Dean’s cheeks at the words. “If you want me to stop, just say ‘Impala.’” Gabriel instructed as a little bit of doubt crept into his mind. “Do you… do you want me to stop?” He asked, needing assurance.

Dean shook his head. “No… God no…”

“Good,” Gabriel replied, his confidence returning. Gabriel’s hands made quick work of the buttons of Dean’s shirt and he pushed it open as far as he could with Dean’s arms already bound. Next, he rucked up Dean’s undershirt, pulling it over his head and leaving it bunched around his elbows. 

Gabriel admired the expanse of skin that was now exposed to him. His mouth descended on Dean, skipping the man’s face and, instead, going straight to his chest. He sucked a bruise into one of Dean’s pectoral muscles before moving to make a matching mark on the other. Then his mouth latched onto one of Dean’s nipples, licking and sucking while his hands went to work on his belt and pants. 

Once they were open, Gabriel pushed Dean’s pants and underwear down as far as he could reach before sitting back and shoving them down further. Dean was still wearing his shoes though, so Gabriel climbed off of the bed, stopping to bite at Dean’s inner thigh, and removed the offending loafers. He pulled Dean’s pants from his body with flair and began the process of removing his own clothes.

Gabriel climbed back onto the bed, dragging his teeth and his nails over the flesh of Dean’s legs, abdomen, and torso as he did so. Once he was about level with Dean again, Gabriel pulled open the latch on a cabinet and practically screeched when a rabbit mask fell out. 

“Jesus, fuck!” He shouted. Then he pushed a button on the wall, speaking clearly into an intercom. “Amelia, three questions: First, how long until we take off? Second, which of my perverted brothers used the jet last? And third, someone did change the sheets afterwards, right?”

“We’re third in line for take off, sir,” came a feminine voice through the intercom, “so it should only be another few minutes. I’d suggest you, ah, buckle up. And everything on board was thoroughly cleaned after Lucifer’s last flight.”

“Of course Luci’s a furry…” Gabriel grumbled before pressing the button again. “Thank you, Amelia. We won’t be needing anything back here for the duration of the flight so you just relax and I can assure you only the bed will need seeing to after we land.”

Gabriel shoved the bunny mask off of the bed and turned back to Dean. “Sorry about that delay. Wasn’t expecting to find my brother’s… costume left behind. Now, where were we?”

Dean’s glazed over look was becoming more lucid and Gabriel couldn’t have that, not so close to take off, so he leaned in and kissed Dean, hard. One hand tugged on his hair while the other played with one of his nipples. He completely dominated the kiss, loving the sounds that Dean was making beneath him. Gabriel quickly rummaged through the cabinet he had opened, grabbing a few items before he latched it shut again.

He kissed his way down Dean’s body, exploring and learning the things that Dean enjoyed. Gabriel was particularly excited to find out how sensitive Dean’s nipples were. He filed that information away for later and continued his journey southward. When he arrived at Dean’s cock, he didn’t touch it with his mouth. Instead, he showed Dean a leather band with two snaps on it. “This is going to help you stay harder longer. I plan on fucking you for the entire flight home so I’ve got one for you and one for me,” he said, holding up a matching band. Gabriel attached the first around Dean’s cock and balls before snapping the other around his own package. 

Next he uncapped the bottle of lube that he had pulled from the closet, wetting two of his fingers. As the plane’s engines sounded, indicating that they were getting ready to take to the air, Gabriel teased Dean’s hole. He felt the aircraft gain momentum and as the wheels left the ground, Gabriel took Dean’s erection into his mouth and slowly pressed his fingers into his ass. Gabriel’s head bobbed on Dean’s cock as his fingers fucked Dean’s hole. It wasn’t preparation, per se, but, rather, the first of many distractions.

When they had reached altitude, Gabriel pulled off of Dean’s cock with a pop. He wiped his fingers off on the bedspread and then ripped open a condom packet. He rolled the latex onto his cock and poured a generous amount of lube into his hand, slicking up his erection. Gabriel grabbed Dean’s ankles and lifted them, putting the man’s legs up onto his shoulders. He lined himself up with Dean’s hole and plunged in. 

His fingers had stretched Dean a little but not enough, Gabriel knew, to fully prepare him to be fucked. That had been the point and from the grunts of “shit” and “fuck” that were coming from Dean’s mouth, it was clear that he was enjoying the roughness. Gabriel immediately began thrusting his hips, loving how deep into Dean he was able to reach in this position. The little room was soon filled with the scent of sweat and sex and the sounds of Gabriel’s balls slapping against Dean’s ass as they both moaned the other’s names.

Gabriel leaned forward, practically folding Dean in half. The change in angle allowed him to brace his hands on the bed, giving him even more leverage and thrust power. Gabriel kissed and bit every inch of Dean’s skin that he could reach, the sounds that Dean was making spurring him on.

Dean’s cock was leaking precum like a fountain.

Gabriel swiped a few fingers across the tip, giving it as little stimulation as he could. “Look at your cock, Dean, look at how much it’s leaking for me,” Gabriel panted. He licked Dean from his fingers, savoring the taste as he continued to fuck into his assistant’s body. “Fuck, just seeing that makes me want to come… I want to come so deep inside of you, Dean. But I’m not gonna, not yet.” 

Gabriel’s hand ran up Dean’s body, his fingernails leaving bright red scratch marks in their wake until he reached Dean’s nipples. He pinched one of them, rolling it between his fingers and Dean cried out, his muscles clamping down on Gabriel’s cock. “Shit, Dean… You could come just from that, couldn’t you? Just from my cock pounding your ass and my fingers tugging on your nipples?”

Dean nodded. “Yes,” he hissed, “fuck yes.”

“Don’t. Don’t you dare come, Dean. Not yet,” Gabriel commanded. “If you’re going to come, you tell me before it happens. You’re going to get one orgasm on this flight and as much as I want this to be good for you, I’m not going to stop fucking you just because it happens early.” Gabriel wasn’t a complete asshole. He knew Dean wasn’t trained to hold back his orgasm so he planned on changing his tactics every time the man got close to cumming. Dean just needed to tell him when that was happening until he could better learn his body. “Can you do that for me, Dean? Be a good boy and tell me when you’re getting close to your orgasm?”

Dean nodded again and Gabriel smiled at the way Dean’s body had responded to the words “good boy,” another thing he’d have to explore more. 

Gabriel went back to work on Dean’s nipples, shifting his position again so that both hands could rest on his chest. Dean’s moans turned into pants and shouts of pleasure as Gabriel tweaked, scratched, and teased the sensitive buds. Each time he ran his fingers over Dean’s nipples or gave them a twist, the muscles in Dean’s ass and pelvis reacted in the most delicious ways. It didn’t take long before Dean was crying out.

“Stop… I’m gonna… I’m so close… stop…”

Gabriel carded a hand through Dean’s hair before giving a sharp tug. “So good for me.” His other hand continued to play with Dean’s nipple for another few seconds before he pulled away and slapped Dean across the face. 

Dean made such a desperate sound that it caused his eyes to shoot open, showing off his lust blown pupils, and it was clear how surprised he was as the moan that had fallen from his lips at being slapped like that. 

One hand still in Dean’s hair, his other hand wandered over his chest and down his torso to his straining erection. Gabriel gave it a few slow strokes before picking up the pace to work in time with his thrusts. 

Even more quickly than with his nipples, Dean was on the verge of cumming again. “Gabe… I’m gonna… please… I’m gonna…”

Gabriel pulled his hand away and slapped Dean again, this time directly on his cock. Another spurt of precum dribbled out at the contact and Gabriel couldn’t help but think that he had hit the jackpot with Dean. Gabriel continued to fuck Dean, all the while toying with his body. He alternated between playing with his nipples and stroking his cock until Dean would beg for release. Eventually, Dean’s sounds just became a stream of pleas as he continuously begged to be allowed to orgasm. Gabriel almost gave in but each time, just before Dean could go over the edge, Gabriel slapped him - always in a different spot - and the pain pulled him back just far enough for the overwhelming urge to subside. Until Gabriel would start the build up again, that is. 

Eventually, Gabriel had to stop fucking Dean or he was going to blow his load too early. It was all well and good because it gave him more space to work and more options on how to keep the man on edge during the flight. Gabriel added tickling and scratching into the mix, and he even occasionally used his mouth on Dean’s cock, running his teeth along the shaft and tip when he thought Dean was getting too comfortable.

The flight to San Francisco had been about four and a half hours but on the smaller, private jet, they could move more quickly and after three hours of non stop stimulation for Dean, a voice came through the intercom. “We’ll be beginning our descent soon, sir. We should be on the ground in about forty five minutes.”

Gabriel knew Amelia wasn’t expecting a response so he didn’t give her one. Instead, he added more lube to his cock and buried himself in Dean’s hole. He set a punishing pace, the break he had taken from fucking Dean making that possible. Every thrust of Gabriel’s hips drew another sound from Dean’s mouth and Gabriel thought that even if the plane went down, just having heard those noises would allow him to die a happy man. 

Gabriel had positioned himself so that he was missing Dean’s prostate, not wanting this to end for Dean quite yet, and he enjoyed the warm tightness that gripped his cock. All the while, Gabriel’s hands and mouth were everywhere on Dean’s body. The man already had multiple deep marks on his neck that Gabriel was pretty sure would last through the weekend and by the time Gabriel was ready to let Dean come, his torso was littered with bruises, scratches, and bite marks. Gabriel thought he looked beautiful. 

Finally, Gabriel repositioned himself so that he could easily reach Dean’s prostate and with each punishing thrust, his cock pounded into the gland, sending sparks and shocks of pleasure through Dean’s body. One of Gabriel’s hands wrapped around Dean’s cock and stroked in time with his thrusts while the other continued to torment one of his already puffy, red nipples. 

“I’m so close… so close Gabe… please… please… pleasepleasepleasepleaseplease….” The words streamed out of Dean’s mouth, spurring Gabriel on. He picked up his pace even more.

“Do it, Dean. Come for me.” They were the same words that Gabriel had spoken to Dean’s sleeping form two nights prior but this time the response was so much better.

Dean cried out as his orgasm rushed through him. Every muscle in his body tensed and then, all at once, exploded with his release. Dean’s cum splattered all over his stomach and chest, some of it even managed to get onto his face and in his hair. 

“Fuck,” Gabe panted as he continued to thrust, drawing Dean’s orgasm out as long as he could. “Fuck, you’re so beautiful when you come, Dean. So fucking beautiful.”

Gabriel pulled out of Dean before he could become over sensitive - that was play for another time, Gabriel decided - and pulled the condom off. He tossed it off the side of the bed, knowing that he was clean. “Open your mouth, Dean,” he commanded, loving how quickly Dean obeyed. 

Gabriel crawled up the bed and straddled Dean’s chest, wiping up some of the man’s cum and popping his fingers into his own mouth, sucking them clean as he pushed himself into Dean’s mouth. 

Dean closed his lips around Gabriel and, despite his limited movement, began giving him one of the best blowjobs he had ever received. 

Gabriel grabbed Dean’s hair, stilling the man’s head. He tugged back a little so that Dean looked up at him with his cock still in his mouth. “You’re good at this,” he commented, running his free hand down Dean’s cheek and swiping his thumb along Dean’s lip. “Such a good little cock sucker. But that’s not what I want right now. Right now, I want to fuck your face so relax your jaw and hold still and if you need me to stop snap your fingers three times. Snap once for me now if you understand.”

Gabriel waited while Dean processed his words and then snapped once, the sharp sound distinct from the noises the plane was making. 

Gabriel grinned down at Dean, pulling back his hips until just the tip of his cock was still in Dean’s mouth. He winked at the man below him and then, without any other warning, he slammed his hips forward, filling Dean’s mouth and pushing into his throat. He continued on like this, having Dean deep throat his cock, until the pressure building in his balls and abdomen were too much. He looked down at Dean, making a spur of the moment decision.

Gabriel pulled all the way out of Dean’s mouth and fisted his cock, Dean’s saliva acting as a lubricant as he furiously stroked himself. He unsnapped the cock ring from around his erection and just as the plane touched down, Gabriel erupted, his cum spraying onto Dean’s face. He couldn’t have timed it better if he had tried.

As the plane taxied along the runway and towards the hangar where it would stay until one of the Shurleys needed or wanted it next, Gabriel unhooked Dean’s arms from the wall, massaging his stiff muscles. He cooed praises into Dean’s ears as he used a warm towel to gently wipe their combined release from Dean’s body.

“We don’t have to get off the plane right away, Dean,” Gabriel told his… whatever it was Dean was to him now. He pulled the blanket out from under Dean and then up and over them before he snaked one of his arms around Dean’s torso. 

Dean tensed at the contact at first but relaxed into it fairly quickly. 

However, when the plane came to a stop, Amelia’s voice rang through the intercom again. “Mr. Shurley, I’m so sorry to interrupt but there’s a car here to take you back to the office. Your father is in the vehicle and I’m told he’s already growing impatient. A second car is here to take Mr. Winchester home.”

Shit. If his dad had flown commercial to come out to Lawrence because Gabriel had requisitioned the jet, he was going to be grumpy at best. Why had he come? Gabriel had said he’d call when he got back but apparently that wasn’t good enough.

Dean pulled away from Gabriel, standing and quickly finding his pants and righting his clothes. 

Gabriel sighed. This was not how this was supposed to go. “I’m sorry, Dean. I thought…” Gabriel’s voice trailed off. He didn’t know what he had thought but it definitely hadn’t been this. He got dressed, too, and followed Dean out of the plane’s bedroom. “I’ll call you tonight,” Gabriel promised just before they disembarked from the plane.

Dean’s cheeks flushed a little, even after everything they had just done, and Gabriel couldn’t help but smile up at him. “Yeah,” Dean replied, “that would be good.”

The two men exited the plane. Gabriel was immediately whisked into the back of a limousine while Dean was directed towards one of the company sedans.


	6. The Hangover

**Summary for the Chapter:**

> Things in the office are tense the Monday following Gabriel and Dean's business trip and Gabriel is determined to figure out why.

**Notes for the Chapter:**

> This chapter fills the hand job square for my kink bingo card. A couple of folks wondered if Gabriel was in trouble after the business trip and this chapter answers that question but not in the way that I think most people are expecting ;)

Gabriel had never been this antsy about going into the office, not since his first day of work at the Lawrence offices, at least. His father had wanted to go over every last detail of the trip with him and then insisted on celebrating well into the night. Mistress Magda and her girls weren’t exactly Gabriel’s idea of a good time but by the time he had been able to get away long enough to call Dean, it was already past midnight. Gabriel hadn’t wanted to wake him up so he’d sent a text instead, asking how he was doing. 

Dean hadn’t responded until the next morning. ‘I’m peachy. See you Monday’ had been the response. Gabriel had texted back, telling Dean to call him if he needed anything but those five words were the only thing he had heard from Dean all weekend.

To say that Gabe was excited to see Dean was an understatement, if his speed as he drove into the office on Monday morning was any indication, and he was grateful that there weren’t any cops along his route. He arrived at the building and scurried up into his office, making two mugs of coffee. He added cream and sugar to his own and took a sip, savoring the flavor.

A few moments later, Gabriel heard Dean outside and went to greet him. 

Dean was just settling in at his desk when Gabriel approached. “Morning,” he greeted. “I made you some coffee!”

Dean turned to look at his boss. His eyes traveled to the mug in his hand and then back to his face. “Oh, I stopped at Starbucks on the way in. I’m good.”

Dean’s voice was flat and the his usually bright green eyes seemed duller somehow. Gabriel pretended not to notice. 

“Not a problem, Dean-o,” he quipped, “just means there’s more for me.” Gabriel winked at Dean but the man responded with a blank stare. 

They stood for a time, an awkward silence growing between them. Finally, they both spoke.

“Dean, what…” Gabriel began at the same time as Dean said “Well, I…”

They both paused and Gabriel indicated that Dean should speak first.

“I was just gonna say that I’ve got a lot of work to get done and that I should get to it.”

Growing up with three older brothers and an eccentric (to say the least) father, Gabriel always knew when he was being dismissed and that was exactly what Dean was doing. The younger man had turned away after he had spoken, logging into his computer and picking up the phone on his desk to check the messages. His back was now towards Gabriel, who stood for another few seconds before turning on his heel and retreating to his office.

Anxiety rose within Gabriel. Something was definitely off and Gabriel had a feeling he knew the root of the problem. But Dean had seemed to enjoy their flight home and then had told Gabriel that all was well the next morning. Gabriel knew that he needed to talk to Dean, needed to figure out exactly what was wrong between them and make an attempt to fix it. 

Around mid-morning, Gabriel called Dean into his office. “Everything going alright out there?” He asked in an attempt to make some small talk.

“Yeah, everything’s fine,” Dean replied. “What do you need, Mr. Shurley?”

The name hurt almost more than the cold shoulder Dean was giving him. “Dean, please, just call me Gabriel.”

“I’d really rather not, Mr. Shurley.”

Gabriel leaned forward in his chair. “Look, Dean, I think…”

Dean cleared his throat. “If you don’t need something, I really should get back to work.” When Gabriel didn’t respond, Dean pursed his lips and nodded once before turning on his heel and leaving the office.

The rest of the day went much the same. Gabriel used the intercom to invite Dean to lunch, Dean replied that he had just placed a take out order. Gabriel asked Dean to come into the office and take notes on a conference call, Dean checked his schedule and caught him in his fib.

Finally, near the end of the day, Gabriel had had it with Dean’s avoidance and cool attitude. Something was definitely wrong and, since Gabriel had already messed things up on the plane, why not go all in and demand answers, he figured.

Decision made, Gabriel marched out of his office, determination coloring his features. Dean was on the phone and Gabriel plucked the receiver out of his hand and hung up with little thought or care for whoever was on the other end of the line. 

“What the hell?” Dean spat. “That was an important call.”

“Then I’m sure they’ll call back,” Gabriel replied, his tone matching Dean’s, “but right now, we need to talk.”

Dean let out a humorless laugh. “We really don’t,” he said, glaring at his boss defiantly. Dean crossed his arms over his chest and pursed his lips. 

“Seriously, Dean, what the hell crawled up your ass and died?” Gabriel asked. He knew he was poking the bear right now, but it was all he could think to do. He needed Dean to talk to him. Even if he couldn’t fix whatever had happened between them, he needed to know for sure what it was. The timing made it clear that it had something to do with their flight home but, beyond that, Gabriel wasn’t sure. Dean had been a willing - and excited - participant in everything they had done. He had been the one moping after Gabriel had called things off on the last night of their trip. He had been the one having the sex dreams. 

“Just forget it, sir,” Dean shot back, refusing to budge. “Go back in your office and let me make my damn call. You’ll have a new assistant by morning; I’ll tell them to send up easiest one they’ve got.”

Dean muttered the last part but Gabriel still heard it, clear as day. 

“Excuse me?” Gabriel asked, his voice incredulous. “What did you just say?”

“I said,” Dean replied, his voice stronger this time, “I’ll tell HR to send up someone easy. That way you won’t have to flirt for a month before you can get into their pants.”

Gabriel was gobsmacked by Dean’s implication. For once in his life, he found himself to be speechless. 

Dean, on the other hand, wasn’t having that problem and he continued on. “That’s what you do, isn’t it? Pretend there’s no other rooms in the hotel so you can seduce and sleep with your assistants? And then get away with it because you’re the boss’s kid? Then you parade in here like nothing happened, acting like you didn’t completely fuck with my… Is that how Charlie got pregnant, sir? Did the help forget to restock the jet with condoms? Does Gil even know he might not be that baby’s father?”

By the time Dean was finished ranting, Gabriel was fuming. He spun Dean’s chair so that the man’s back was to him and he bent over so that he could speak directly into Dean’s ear. He gripped his assistant’s hair tightly in one hand and pulled his head back just a little bit. “Dean Winchester lower your voice,” he commanded. “You have no idea what you’re talking about and, unless you want to find yourself the subject of office gossip and ridicule, you will keep your voice down.”

A whimper escaped Dean’s lips and his breathing picked up.

“Understand this, Dean: I have never slept with an employee before this weekend. You. You are the only one. You do this to me,” Gabriel snarled as he grabbed one of Dean’s hands and moved it to his crotch. Despite the tone of their conversation, Gabriel was hard and he wanted - needed - Dean to know it. “Unlike you and I, men don’t do a thing for Charlie. Gil is short for Gilda, you ass.”

Gabriel released Dean’s hand and began to work on his belt, pulling his assistant’s cock out of his pants. He began to stroke Dean, who was already half hard, with a dry hand. “You want me to stop, you say the word,” he hissed into Dean’s ear, “and we go back to how things were. You can transfer back downstairs if you want or stay here. I’ll keep it completely professional, if that’s what you want. One word and I stop. But do you know what I think? I think you like this. I think you like being at my mercy, submitting to my desires over your own.”

The phone rang. 

“Answer it. On speaker phone,” Gabriel hissed into Dean’s ear.

Dean reached forward but Gabriel didn’t move either of his hands. One was still threaded through Dean’s hair, his movement toward the phone pulling at the strands making him groan. Gabriel’s other hand continued to work his cock and Dean appeared to steel himself for whatever phone call was about to take place. 

“Gabriel Shurley’s office,” he greeted, his voice just a little bit breathy. 

“Mr. Winchester,” the voice on the other end responded, “this is Garth down in HR. I believe we got disconnected a few moments ago, while we were talking about how to best facilitate a transfer back down to the front desk. We should be able to handle that today, you’d be back in your old job first thing in the morning.”

Gabriel didn’t know Garth well but he knew he was a kind man and he made a mental note to make sure his next bonus had a little extra included in it, especially if Dean didn’t make it through this phone call without embarrassing himself. Garth hadn’t asked to end up in the middle of their spat, after all, but here he was unknowingly listening in as Gabriel stroked Dean’s erection.

With every downstroke, Gabriel fondled Dean’s balls some and, whenever he reached the tip, he smeared the precum around and paid special attention to the ridge just below the head of his cock. His movements were slow and methodical and Gabriel could tell it was taking every ounce of Dean’s control to stay quiet and not buck up into his hand. So much of his attention was focused on those things, that he didn’t respond to Garth.

“Mr. Winchester?” the man asked, then they heard his voice muffled. “I think something’s wrong with my phone again, Bobby. We might need to get IT back out here.”

Gabriel gave Dean’s hair a pull and shot a pointed look towards the phone. 

“I’m… I’m here, Garth,” Dean said, swallowing the gasp that had threatened to escape. “Sorry about that. Yeah, uh, we got disconnected but…” Dean had to pause, his mouth open wide in a silent scream as Gabriel twisted his hand around his cock. “...But don’t worry about it,” he rushed out before biting down on his lower lip, the tiniest whine slipping out of his mouth. Dean was gripping the armrests of his chair so tightly his knuckles were white. He took a deep breath to steady himself as best as he could. “I don’t need that transfer anymore. Thanks, Garth. Have a good day.”

Dean reached forward to end the call so quickly that it made Gabriel chuckle. “So, you’re staying?” he asked, his breath hot against his assistant’s ear.

“Yes, sir,” Dean hissed, his eyes screwed shut as he finally allowed himself to feel the full brunt of the pleasure that had been building in his body.

Gabriel didn’t let up, his hand relentlessly working Dean’s cock. “Good,” he replied, “I don’t want another assistant. I want you, Dean. In every way.” He sucked Dean’s earlobe into his mouth and ran his teeth over the flesh.

Dean shuddered in Gabriel’s arms. He was unable to contain the whimpers and mewls that fell from his lips and, as Gabriel picked up speed, his hips started bucking up into his fist and his head lolled back onto Gabriel’s shoulder. Dean’s jaw hung open and his breathing came in shallow pants. 

“Come for me, Dean,” Gabriel commanded with a twist of his wrist.

Within seconds, Dean’s orgasm hit him. He let out a long, low moan and his body tensed up before releasing all at once as cum spurted from his cock, running down over Gabriel’s hand. 

Gabriel stroked Dean through his orgasm, smearing his cum around his erection. Once Dean was finished, he pulled a few tissues from a box that was sitting on the man’s desk and gently wiped him clean. “Put your dick away and come meet me in my office.” Gabriel’s voice was softer, kinder even, but there was still no room for argument as he released Dean’s softening cock and returned to his office.

Dean followed not too far behind. His cheeks were still pink and his breathing hadn’t quite returned to normal by the time he entered Gabriel’s office. 

Gabriel was waiting for him on the rarely used couch that adorned one of the walls, a bottle of water and a package of crackers on the table in front of him. “Close the door and come sit with me.”

Dean did as he was asked, crossing the room and sitting on the opposite side of the couch, his body rigid as if he might need to jump up and run at any second. 

Gabriel slid across the couch so that he was beside Dean. “For someone who just had an orgasm, you sure are tense,” he joked. One of his hands landed on Dean’s shoulder and the other reached to grab the water. He handed it to Dean. “Drink some of this.” Once Dean obliged, Gabriel carded his fingers through Dean’s hair. The angle was awkward but Dean clearly wasn’t comfortable quite yet so he made do. It was something they’d have to work on if this was going to continue.

“Not that it matters,” Gabriel began, “but for the record, Charlie is gay. Gil is short for Gilda, her wife’s name.”

Dean grunted in reply.

The pair sat together in silence for a while, Gabriel stroking Dean’s hair and Dean staring straight ahead, until the younger man started to relax. 

“Dean, I’m going to ask you a question and I need you to answer me honestly, okay?”

Dean chanced a look at Gabriel before licking his lips and nodding. 

“What happened this weekend?” 

Dean’s jaw clenched and he closed his eyes. Slowly the muscles there relaxed and Gabriel thought that he might be making a conscious effort to do so. “After we… flew home,” Dean began slowly, clearly choosing his words carefully, “you said you’d call that night. When you didn’t, when I woke up to a couple of words in a text message… I don’t know, man. I’ve had sex with people, topped and bottomed plenty of times but it’s never… never been like that. That was just… I don’t know. And then you didn’t call and it all just messed with my head, I guess.”

“You dropped,” Gabriel whispered. He wanted to rant and rave and curse - all at himself - but that wouldn’t do Dean any good so he forced himself to remain calm, the hand in Dean’s hair only faltering for a second or two before it resumed its petting. “Dean, had you ever done anything like that, like what we did on the plane, before Friday? Mixed pleasure and pain like that or even been tied up?” Gabriel’s mind was whirling and it threatened to spiral when Dean shook his head ‘no.’ “Oh, Dean-o, I am so sorry. I should have called. Hell, I shouldn’t have let us get off of that plane in the first place, not until I knew that you were going to be alright, my father’s impatience be damned.”

While he was talking Gabriel moved to sit in Dean’s lap, straddling his upper legs and looking into his eyes. “Dean, I know I’ve only known you a month but you are hard working, you are loyal, you are incredibly sharp, and I let you down on Friday.” Gabriel paused and licked his lips. “I meant it out there, Dean. I want you in every way - you’re an amazing assistant but I want more than that. I sure as hell don’t deserve more than that but I still want it. I want to take you on dates, I want to have you on my arm at fundraiser dinners, charity balls, and other terribly boring functions, I want to show you off to my friends. But I also want to tie you down and fuck you raw. I want to take control of your body and, to an extent, your mind. I want you to be mine in every sense of the word.”

Gabriel watched as Dean swallowed hard. Dean’s eyes were hooded and Gabriel could feel his cock filling again beneath where he sat. That part of him, at least, was interested in what Gabriel was saying. 

“I… I want…” Dean began, his mouth obviously dry.

Gabriel grabbed the water bottle from him and held it to his lips, encouraging him to drink. “I want to take care of you, Dean.”

Dean nodded. “I’ve never… Can we take it slow?”

Gabriel smiled. “Sure thing, kiddo.” He leaned in and gently kissed Dean. He could do slow or, at least, he could try. He owed Dean at least that much. “If we’re going to do this, I want to do it right. How does dinner sound?”

**Author's Note:**

> Thank you for reading! This is currently an ongoing project so comments and kudos will be especially helpful to me! I’m not going to withhold chapters until I get a certain count - that’s not my style - but it definitely helps spur on my creativity when I know people are enjoying something I’m working on! <3 <3


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